Crossdressing Not Going Out19

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Reading your post, we’re pretty much in the same position. The only differences (i believe, but you can tell me otherwise) that may be a factor are:-
1/ My wife knows but is unsupportive
2/ I used to travel a lot with work.
So I am used to going out and about solo and have encountered many different situations, some good and some bad, from which you learn to deal with. Mainly by trial and error on my part.

I was going to suggest the same as Katie, with late-night walks but on your own, to build up your confidence. as you regain confidence, pop into a late-night supermarket, to slowly engage with others or attend an event, like BNO, if you want a more friendly environment.